2.0 2012-07-30 14:55:17 -0600 2015-06-03 17:21:08 -0600 ECMDB21310 M2MDB001713 Bis-molybdopterin guanine dinucleotide Bis-molybdopterin guanine dinucleotide is a member of the chemical class known as Purine Ribonucleoside Diphosphates. These are purine ribobucleotides with diphosphate group linked to the ribose moiety. <i>bis</i>-molybdopterin guanine dinucleotide MGD Molybdopterin guanine dinucleotide MoO2(OH)Dtpp-mGDP MoO₂(OH)Dtpp-mGDP MPT-GMP C20H28MoN10O15P2S2 870.51 871.970632526 molybdenum(2+) ion 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[({[({2-imino-4-oxido-6,7-disulfanyl-1H,2H,5H,5aH,8H,9aH,10H-pyrano[3,2-g]pteridin-8-yl}methyl phosphonato)oxy]phosphinato}oxy)methyl]oxolan-2-yl]-2-imino-3,4,5,9-tetrahydro-2H-purin-6-olate dihydrate molybdenum(2+) ion 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-({[({2-imino-4-oxido-6,7-disulfanyl-1H,5H,5aH,8H,9aH,10H-pyrano[3,2-g]pteridin-8-yl}methyl phosphonato)oxyphosphinato]oxy}methyl)oxolan-2-yl]-2-imino-4,5-dihydro-3H-purin-6-olate dihydrate O.O.[Mo++].[H][C@]1(COP([O-])(=O)OP([O-])(=O)OCC2([H])OC3([H])NC4=C(NC3([H])C(S)=C2S)C([O-])=NC(=N)N4)O[C@@]([H])(N2C=NC3([H])C([O-])=NC(=N)NC23[H])[C@]([H])(O)[C@]1([H])O InChI=1S/C20H28N10O13P2S2.Mo.2H2O/c21-19-26-13-7(15(33)28-19)24-6-12(47)11(46)5(41-17(6)25-13)2-40-45(37,38)43-44(35,36)39-1-4-9(31)10(32)18(42-4)30-3-23-8-14(30)27-20(22)29-16(8)34;;;/h3-6,8-10,14,17-18,24,31-32,46-47H,1-2H2,(H,35,36)(H,37,38)(H3,22,27,29,34)(H4,21,25,26,28,33);;2*1H2/q;+2;;/p-4 PNPXRABSZIPVFU-UHFFFAOYSA-J Cytoplasm logp -4.9 ChemAxon pka_strongest_acidic -4.3 ChemAxon pka_strongest_basic 15.3 ChemAxon iupac molybdenum(2+) ion 9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[({[({2-imino-4-oxido-6,7-disulfanyl-1H,2H,5H,5aH,8H,9aH,10H-pyrano[3,2-g]pteridin-8-yl}methyl phosphonato)oxy]phosphinato}oxy)methyl]oxolan-2-yl]-2-imino-3,4,5,9-tetrahydro-2H-purin-6-olate dihydrate ChemAxon average_mass 870.51 ChemAxon mono_mass 871.970632526 ChemAxon smiles O.O.[Mo++].[H][C@]1(COP([O-])(=O)OP([O-])(=O)OCC2([H])OC3([H])NC4=C(NC3([H])C(S)=C2S)C([O-])=NC(=N)N4)O[C@@]([H])(N2C=NC3([H])C([O-])=NC(=N)NC23[H])[C@]([H])(O)[C@]1([H])O ChemAxon formula C20H28MoN10O15P2S2 ChemAxon inchi InChI=1S/C20H28N10O13P2S2.Mo.2H2O/c21-19-26-13-7(15(33)28-19)24-6-12(47)11(46)5(41-17(6)25-13)2-40-45(37,38)43-44(35,36)39-1-4-9(31)10(32)18(42-4)30-3-23-8-14(30)27-20(22)29-16(8)34;;;/h3-6,8-10,14,17-18,24,31-32,46-47H,1-2H2,(H,35,36)(H,37,38)(H3,22,27,29,34)(H4,21,25,26,28,33);;2*1H2/q;+2;;/p-4 ChemAxon inchikey PNPXRABSZIPVFU-UHFFFAOYSA-J ChemAxon polar_surface_area 349.13 ChemAxon refractivity 209.14 ChemAxon polarizability 62.59 ChemAxon rotatable_bond_count 9 ChemAxon acceptor_count 20 ChemAxon donor_count 10 ChemAxon physiological_charge -1 ChemAxon formal_charge -2 ChemAxon guanylyl molybdenum cofactor biosynthesis The transition element molybdenum (Mo) has been long known as an essential micronutrient across the kingdoms of plants, animals, fungi and bacteria. However, molybdate itself is catalytically inactive and, with the exception of bacterial nitrogenase, needs to be activated through complexation by a special cofactor. There are several molybdenum cofactors, including molybdopterin (MPT), guanylyl molybdenum cofactor (MGD), cytidylyl molybdenum cofactor, or others [Rajagopalan92]. The chemical nature and biosynthesis of molybdenum cofactors have been investigated in detail in bacteria [Wuebbens95, Pitterle93, Pitterle93a, Rajagopalan92, SantamariaArauj04] and plants [Schwarz06]. All of the cofactors are synthesized from molybdopterin (MPT). The MPT structure is conserved in all organisms and it has been demonstrated that its biosynthesis is preserved in bacteria and plants alike. It is produced from GTP via cyclic pyranopterin phosphate (see molybdenum cofactor biosynthesis). The variability of the molybdenum cofactors found in bacteria is achieved by the attachment of GMP, AMP, IMP, or CMP to the phosphate group of MPT. In Escherichia coli, both guanylyl molybdenum cofactor and cytidylyl molybdenum cofactor are present. bis(molybdenum cofactor) synthase [multifunctional] catalyzes the transfer of the guanine nucleotide from GTP, releasing the β- and γ-phosphates of GTP as pyrophosphate and forming guanylyl molybdenum cofactor. (EcoCyc) PW002032 Metabolic guanylyl molybdenum cofactor biosynthesis PWY-5964 50986239 CPD-582 Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 Molybdopterin-guanine dinucleotide biosynthesis protein A P32173 MOBA_ECOLI mobA http://ecmdb.ca/proteins/P32173.xml Molybdopterin-guanine dinucleotide biosynthesis protein B P32125 MOBB_ECOLI mobB http://ecmdb.ca/proteins/P32125.xml bis-molybdopterin mono-guanine dinucleotide + Guanosine triphosphate + Hydrogen ion > Bis-molybdopterin guanine dinucleotide + Pyrophosphate Bis-molybdopterin guanine dinucleotide + Guanosine triphosphate + Hydrogen ion + Molybdopterin guanine dinucleotide > Guanylyl molybdenum cofactor + Pyrophosphate PW_R005942